Herbicidal 3-substituted-phenyl-1,2,3-benzotriazin-4-ones

ABSTRACT

This invention relates to 3-substituted-phenyl-1,2,3-benzotriazin-4-ones which have activity as herbicides, to compositions which contain these compounds and to methods of use of these compounds.

This invention relates to 3-substituted-phenyl-1,2,3-benzotriazin-4-oneswhich have activity as herbicides, to compositions which contain thesecompounds and to methods of use of these compounds.

BACKGROUND OF INVENTION

Certain 3-(2-halophenyl)-1,2,3-benzotriazin-4-ones have been disclosedas antisecretory agents (DE 2012094), or anticonvulsant agents (DE1271118). Other benzotriazinylbenzoic acid and benzotriazinylbenzoateshave been disclosed as agrochemical fungicides (DD 241075). There is nosuggestion in any of these disclosures that such compounds areherbicidal.

We have discovered a class of 1,2,3-benzotriazin-4-ones which, ratherthan acting as fungicides, act as selective herbicides. Although a widevariety of herbicidal compounds and compositions are known for thecontrol of unwanted vegetation, the need continues for novel andimproved herbicidal compounds and compositions. This is particularlytrue for situations wherein a crop is infested with botanically similarweeds, for example, when a crop such as corn is infested with grassyweeds. In addition, weeds can become resistant to known herbicides overtime. To overcome such resistance, economic and environmentalconsiderations often favor herbicides having different modes of actionthan those currently used. There remains, therefore, a need forherbicidal agents which are as effective or more effective thanpresently existing compounds.

SUMMARY OF THE INVENTION

The present invention relates to herbicidal compounds and methods fortheir use in controlling unwanted plant species and their use inherbicidal compositions in agriculture. In particular, the presentinvention pertains to compounds containing a substituted phenyl ringlinked to a 1,2,3-benzotriazin-4-one heterocyclic ring.

We have found that certain compounds of this invention are useful aspre-emergent and post-emergent herbicides. These compounds arerepresented by formula I

wherein

m is 1 to 4;

R₁ is hydrogen, halo, (C₁-C₄)alkyl, (C₁-C₃)haloalkyl, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, nitro, cyano, phenoxy, or phenoxy substituted withhalo, (C₁-C₃)alkyl, (C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, or cyano;

X₁ is hydrogen, halo, or acetyl;

X₂ is hydrogen or halo;

X₃ is halo, cyano, or nitro;

X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkylamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy;

X₅ is hydrogen or halo;

provided that:

a) when X₁ is halo or acetyl and X₂ and X₅ are hydrogen, then X₃ and X₄form a 5- or 6-membered heterocyclic ring fused to the phenyl ringstructure to form a bicyclic moiety having the structure

wherein

L is oxygen (O) or sulfur (S);

R₂ is hydrogen or alkyl;

R₃ is hydrogen; (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl; (C₁-C₆)alkoxyalkyl; (C₃-C₆)alkenyloxyalkyl;(C₃-C₆)alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy;

R₄ is hydrogen, (C₁-C₃)alkyl, or fluorine; or

b) when X₁ and X₃ are halo and X₂ is hydrogen, then X₄ and X₅ form a 5-or 6-membered heterocyclic ring fused to the phenyl ring structure toform a bicyclic moiety having the structure

wherein

Y is oxygen, sulfur or a group of —NR₆ in which R₆ is hydrogen,(C₁-C₆)alkyl, (C₃-C₅)alkenyl or (C₃-C₆)alkynyl;

Y′ is oxygen, sulfur, a group of —NR₆, or a group of —CO;

R₅ is hydrogen, halo, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl, (C₂-C₆)alkenyl,or (C₃-C₆)alkynyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, cyano, (C₁-C₆)hydroxyalkyl, a group of —CO₂R₈, a formyl group, an acyl group,(C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, or a carboxyl group;

R₆ is hydrogen, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, or (C₃-C₆)alkynyl;

R₇ is hydrogen, halo, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, an acyl group, ora nitro;

and agronomically acceptable salts thereof.

The term “alkyl” includes both branched and straight chain alkyl groups.Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl,isooctyl, nonyl, decyl, undecyl, dodecyl and the like.

The term “cycloalkyl” refers to a cyclic aliphatic ring structure suchas cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane,cyclooctane and the like.

The term “haloalkyl” refers to an alkyl group substituted with one ormore halo groups.

The term “halo” refers to fluoro, chloro, bromo or iodo.

The term “alkylsulfonylalkyl” refers to an alkyl group substituted withan alkylsulfonyl (alkyl-SO₂) group, for example methylsulfonylmethyl.

The term “alkylsulfinylalkyl” refers to an alkyl group substituted withan alkylsulfinyl (alkyl-SO) group, for example methylsulfinylmethyl.

The term “alkenyl” refers to an ethylenically unsaturated hydrocarbongroup, straight or branched, having 1 or 2 ethylenic bonds.

The term “haloalkenyl” refers to an alkenyl group substituted with oneor more halo groups.

The term “alkynyl” refers to an unsaturated hydrocarbon group, straightor branched, having 1 or 2 acetylenic bonds.

The term “alkoxy” includes both branched and straight chain alkyl groupsattached to a terminal oxygen atom. Typical alkoxy groups includemethoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy and the like.

The term “haloalkoxy” refers to an alkoxy group substituted with one ormore halo groups.

The term “alkylthio” includes both branched and straight chain alkylgroups attached to a terminal sulfur atom.

The term “haloalkylthio” refers to an alkylthio group substituted withone or more halo groups.

Acceptable acids that may form agronomically acceptable salts of thecompounds of the present invention include, for example, hydrochloricacid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid,phosphoric acid, oxalic acid, acetic acid, propionic acid, glycolicacid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid,(C₂-C₂₀)alkylbenzenesulfonic acid, sodium hydrogen sulfate and methylhydrogen sulfate.

Other agronomically acceptable salts may be formed by complexation ofthe compounds of the current invention with metal salts such as zincchloride or iron chloride.

Preferred compounds include compounds of the formula

wherein

m is 1 to 4;

R₁ is hydrogen, halo, (C₁-C₄)alkyl, (C₁-C₃)haloalkyl, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, nitro, cyano, phenoxy, or phenoxy substituted withhalo, (C₁-C₃)alkyl, (C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, or cyano;

X₁ is hydrogen, halo, or acetyl;

X₂ is hydrogen or halo;

X₃ is halo, cyano, or nitro;

X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkylamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy;

X₅ is hydrogen or halo;

and agronomically acceptable salts thereof.

Even more preferred compounds include compounds of the formula

wherein

m=1 to 4;

R₁ is hydrogen, halo, (C₁-C₄)alkyl, (C₁-C₃)haloalkyl, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, nitro, cyano, phenoxy, or phenoxy substituted withhalo, (C₁-C₃)alkyl, (C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy,(C₁-C₃)haloalkoxy, or cyano;

L is O or S;

X₁ is H, Cl or F

R₂ is H or (C₁-C₃)alkyl; and

R₃ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl,halo(C₃-C₆)alkenyl, (C₃-C₆)alkynyl; halo(C₃-C₆)alkynyl, alkoxyalkyl;alkenyloxyalkyl; alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; andagronomically acceptable salts thereof.

General Synthetic Methods

The compounds of formula I of the present invention can be prepared bythe following processes:

Benzoic acids (when X is hydroxy) or their acyl chlorides (when X ischloride) II are reacted with anilines III in a solvent such aschloroform, dichloromethane, carbon tetrachloride, hexane, benzene,toluene, tetrahydrofuran, dioxane, acetone or methyl ethyl ketone toyield compounds IV, optionally in the presence of the bases such asEt₃N, pyridine, NaOH, KOH, Na₂CO₃, K₂CO₃, NaHCO₃ at a temperature from−40° C. to the boiling point of the solvent for 3 minutes to 48 hours.

Anilines may be obtained from the nitro substituted benzene (made byknown methods such as those described in EP 0 083 055 A2) by reactingwith hydrogen or reductive metals such as, for example, iron, zinc, andtitanium, etc. in compatible solvents, such as chloroform,dichloromethane, carbon tetrachloride, hexane, benzene, toluene,tetrahydrofuran, dioxane, acetone, methyl ethyl ketone, ethanol orcombined with an inorganic acid such as hydrochloric acid, at atemperature from −40° C. to the boiling point of the solvent for 3minutes to 48 hours.

Intermediate V from IV may employ similar procedures to prepare anilinesIII.

Intermediate V also may be obtained from the following reactions:

Intermediates VII may be obtained from reacting VI with anilines III ina solvent such as chloroform, dichloromethane, carbon tetrachloride,hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone or methylethyl ketone to yield compounds VII, optionally in the presence of thebases such as Et₃N, pyridine, NaOH, KOH, Na₂CO₃, K₂CO₃, NaHCO₃ at atemperature from −40° C. to the boiling point of the solvent for 3minutes to 48 hours.

Intermediates VII are reacted with an inorganic acid such ashydrochloric acid without or in an organic solvent such as chloroform,dichloromethane, carbon tetrachloride, hexane, benzene, toluene,tetrahydrofuran, dioxane, acetone or methyl ethyl ketone to yieldintermediates IV at a temperature from ambient temperature to theboiling point of the solvent for 3 minutes to 48 hours.

Intermediates IV are reacted with nitrous acid in a solvent such aswater, chloroform, dichloromethane, carbon tetrachloride, hexane,benzene, toluene, tetrahydrofuran, dioxane, acetone or methyl ethylketone to yield compounds I at a temperature from −40° C. to the boilingpoint of the solvent for 3 minutes to 48 hours.

Certain compounds of the Formula I may be obtained by reacting compoundsof the Formula I-1, which can be prepared according to Scheme 1 withalkyl halides or alkyl sulfonylesters in a solvent inert under thereaction conditions, e.g., chloroform, dichloromethane, carbontetrachloride, hexane, benzene, toluene, ethyl acetate, acetone,dimethylformamide, tetrahydrofuran or dioxane, optionally in thepresence of a base such as triethylamine, pyridine, sodium hydroxide,potassium hydroxide, sodium carbonate, potassium carbonate, sodiumbicarbonate or sodium hydride at a temperature from −40° C. to theboiling point of the solvent for 3 minutes to 48 hours. Alkyl halides oralkyl sulfonylesters are commercially available or can be prepared byknown methods.

Examples of compounds of the Formula I, prepared according to the abovegeneral methods, are listed in Table 1a, Table Ib and Table 2. Thepreparation of several specific examples in this invention is describedbelow in more detail.

1. Preparation of Compound No 49

A solution of 2-nitro-benzoyl chloride (2.04 g, 90% purity, 10 mmol) inCH₂Cl₂ (20 mL) was added dropwise into a mixture of7-fluoro-6-amino-2H-1,4-benzoxazin-3-(4H)-one (1.78 g, 10 mmol) andtriethylamine (1.1 g, 11 mmol) in CH₂Cl₂ (20 mL) over 10 min withice-water bath cooling. The reaction mixture was then stirred at roomtemperature overnight. The mixture was poured into water and theresulting precipitate was collected by suction-filtration and washedwith hexane and then water to give7-fluoro-6-(2-nitrobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-one, 2.9 g(yield: 92%) as a solid: mp >248° C.

A solution of 2 N NH₄Cl (15 mL, 27 mmol) was added into a solution ofthe above intermediate (1.1 g, 3.4 mmol) in THF (25 mL) in an ice-waterbath. Zinc dust (1.5 g, 16 mmol) was added portionwise over 15 min. Thereaction mixture was stirred at room temperature for 3 h and then theinsoluble materials were removed by suction-filtration and washed withEtOAc and water. The filtrate was extracted with EtOAc and the combinedorganic layer was washed sequentially with water and brine. The organicextracts were dried over Na₂SO₄ and filtered. After removing thesolvents by evaporation,7-fluoro-6-(2-aminobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-one (0.7 g,70%) was obtained as a solid: mp 251-252° C.

A solution of 3 N NaNO₂ (0.6 mL, 2.6 mmol) was added into a slurry of7-fluoro-6-(2-aminobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-one (0.6 g, 2mmol) in 2 N HCl (7 mL) with stirring in an ice-water bath. The reactionmixture was stirred at room temperature for 3 h and the resultingprecipitate was collected by suction-filtration and washed with water.The compound,3-[7-fluoro-2H-1,4benzoxazin-3(4H-one-6]-1,2,3-benzotriazin-4-one (0.55g, 90%) was obtained as a solid: mp >252° C.

2. Preparation of Compound 62

Sodium hydride (0.070 g 60% in oil, 1.8 mmol) was added into a mixtureof compound 49 (0.45 g, 1.5 mmol) in DMF (15 mL) with stirring in anice-water bath. The reaction mixture was stirred at room temperature for10 min and then propargyl bromide in toluene (0.25 g, 80%, 1.6 mmol) wasadded. The reaction mixture was stirred at room temperature overnightand then combined with EtOAc (100 mL), washed sequentially with waterand brine, and dried over Na₂SO₄. The titled compound,3-[7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H-one-6]-1,2,3-benzotriazin-4-one,0.3 g yield: 60%) was obtained as a solid after solvents were removed invacuum, mp 246-248° C.

TABLE 1a

No R₁ X_(l) X₂ X₃ X₄ X₅ mp (°C.) 1 H H H H H H 149-150 2 H F H H H H140-141 3 H Cl H H H H 116-117 4 H Br H H H H 105-106 5 H I H H H H148-149 6 H CH₃ H H H H 163-164 7 H CF₃ H H H H 143-144 8 H CN H H H H158-159 9 H CH₃O H H H H 150-151 10 H H F H H H 133-134 11 H H Cl H H H140-141 12 H H Br H H H 156-157 13 H H I H H H 143-144 14 H H CH₃ H H H148-149 15 H H CF₃ H H H 134-135 16 H H CN H H H 192-193 17 H H CH₃O H HH 123-124 18 H H H F H H 147-148 19 H H H Cl H H 183-184 20 H H H Br H H194-195 21 H H H I H H 134-135 22 H H H CH₃ H H 138-139 23 H H H CF₃ H H231-232 24 H H H CN H H 226-227 25 H H H CH₃O H H 155-156 26 H F H Cl HH 144-145 27 H Cl H Cl H H 125-126 28 H Cl H F H H 174-175 29 H CH₃ H HCH₃ H 30 H CH₃ H CH₃ H H 126-127 31 H H Cl Cl H H 210-211 32 H H Cl H ClH 219-220 33 H F H F F H 168-169 34 H F H CN F H 203-205 35 H Cl H F CH₃H 157-158 36 H F H Cl cyclopentyloxy H 133-134 37 H F H Cl propargyloxyH 185-186 38 H F H Cl C₂H₅OCO₂— H 128-129 39 H F H Cl (CH₃)₂CH₂OCO— H183-184 40 H F H Cl C₂H₅OCOCH₂O— H 118-120 41 H Cl H Cl propargyloxy H151-152 42 8(7?)-Cl F H Cl propargyloxy H 158-160 43 5-CH₃ F H Clpropargyloxy H oil 44 7-CF₃ F H Cl propargyloxy H 124-125 45 6-A* F H ClH H 153-154 46 H F H F H F 173-174 47 H Cl H Cl H Cl 126-127 48 H Br HBr H Br 128-129 *A =

TABLE 1b Compound No Structure mp(°C.) 49

>252 78

208-209 79

203-204

TABLE 2

No R₁ R₂ mp (°C.) 49 H H >252 50 H CH₃ 255-257 51 H C₂H₅ 222-224 52 HNCCH₂ 240-242 53 H FCH₂CH₂ 215-217 54 H CF₃CH₂ 243-245 55 H ClCH₂CH₂190-192 56 H BrCH₂CH₂ 219-220 57 H CH₃OCH₂ 213-215 58 H CH₃SCH₂ 204-20759 H CH₃CH₂CH₂ 174-176 60 H allyl 212-214 61 H 2-chloroallyl 195-197 62H propargyl 246-248 63 H CH₃CH(CN) 165-170 64 H FCH₂CH₂CH₂ 184-186 65 HCICH₂CH₂CH₂ 129-131 66 H CHF₂CF₂CH₂ 195-197 67 H CH₃OCH₂CH₂ 196-199 68 HCH₃CH₂OCH₂ 178-180 69 H CH₃CH₂CH₂CH₂ 160-162 70 H (CH₃)₂CHCH₂ 180-182 71H 2-CH₃-allyl 200-202 72 H 1-CH₃-propargyl 95-97 73 H 2-butynyl 248-25074 H C₂H₅OCOCH₂ 174-176 75 H CH₃CH₂CH₂CH₂CH₂ 131-133 76 H 2-pentynyl190-192 77 7-CF₃ H 157-158

Herbicidal Activity

When a compound of formula I of the present invention is used as anherbicide, the active ingredient can be used in a suitable formulationdepending upon the particular purpose and by a suitable applicationmethod. Usually, the active ingredient is diluted with an inert liquidor solid carrier, and used in the form of a formulation such as a dust,a wettable powder, an emulsifiable concentrate, aqueous or oilsuspension, pellets, granules, etc., If desirable one may also add oneor more surfactants and/or other additives. Furthermore, one of ordinaryskill in the art will recognize that a compound of the present inventionmay be used in combination with an insecticide, a nematocide, afungicide, other herbicides, a plant growth controlling agent, afertilizer, etc.

The compounds of the present invention can be used in the form ofcompositions or formulations. Examples of the preparation ofcompositions and formulations can be found in the American ChemicalSociety publication “Pesticidal Formulation Research,” (1969), Advancesin Chemistry Series No. 86, written by Wade Van Valkenburg; and theMarcel Dekker, Inc. publication “Pesticide Formulations”, (1973) editedby Wade Van Valkenburg. In these compositions and formulations, theactive substance is mixed with conventional inert agronomicallyacceptable (i.e., plant compatible and/or pesticidally inert) pesticidediluents or extenders such as solid carrier materials or liquid carriermaterials, of the type usable in conventional pesticide compositions orformulations. By “agronomically acceptable carrier” is meant anysubstance which can be used to dissolve, disperse of diffuse the activeingredient in the composition without impairing the active ingredient'seffectiveness and which by itself has no significant detrimental effecton the soil, equipment, desirable plants, or agronomic environment. Ifdesired, adjuvants such as surfactants, stabilizers, antifoam agents andanti-drift agents may also be combined. Such adjuvants commonly used inthe art can be found in McCutcheon's Emulsifiers and Detergents,McCutcheon's Emulsifiers and Detergents/Functional Materials, andMcCutcheon's Functional Materials all published annually by McCutcheonDivision of MC Publishing Company (New Jersey) and Farm ChemicalsHandbook published by Meister Publishing Company (Ohio). Compositionsand formulations according to the present invention may also includeother known pesticidal compounds. This expands the spectrum of activityof the preparation and may give rise to synergism.

The formulations may contain from about 0.1% to 99% by weight of activeingredient(s) and at least one of (a) 0.1% to 20% surfactant(s) and/or(b) 1% to 99.9% solid or liquid diluent(s).

If the compound of formula(I) is formulated with an additionalherbicide, the concentration of active ingredient(s) in the compositionscan vary within a wide range, depending on the active compound, theapplications for which they are destined, the environmental conditions,and the kind of formulation. The concentration of active ingredient(s)in the compositions is generally between 1% to 95%, preferably between5% to 60%. In use, unwanted vegetation is controlled by applying to thevegetation, or to the soil wherein the unwanted vegetation grows, anherbicidally effective amount of a compound of formula I or acomposition comprising one or more compounds of formula I and anagronomically acceptable carrier. The compounds and compositions of thisinvention can be diluted or applied as is to plant foliage and/or soilas aqueous sprays by methods commonly employed, such as conventionalhigh-volume hydraulic sprays, low-volume sprays, air-blast, and aerialsprays. The dilution and rate of application will depend upon the typeof equipment employed, the method and frequency of application desired,the herbicide application rate, and the weeds to be controlled. Thecompositions can be mixed with fertilizers or fertilizing materialsbefore their application.

The effective dose of the compounds of the present invention is usuallywithin a range of from 1 g/ha to 3 kg/ha, preferably from 5 g/ha to 500g/ha.

The following examples illustrate several aspects of this invention indetail:

Biological Testing

Listed below, a typical planting design for the test, consisting of fourmonocot weeds, four dicot weeds and one sedge weed.

Common Name Scientific Name Grasses Barnyardgrass Echiniochloa crusgalliCrabgrass (large) Digitaria sanguinalis Foxtail, (green) Setaria viridisPerennial Ryegrass Lolium perenne Sedges Nutsedge, (yellow) Cyperusesculentus Broad Leaf Weeds Hairy Beggarticks Bidens pilosa Nightshade,(black) Solanum nigrum Smartweed, (pale) Polygonum lapathifoliumVelvetleaf Abutilon theophrasti

For each compound, evaluation tests were carried out according to thefollowing procedures:

For preemergence tests, immediately after planting, the test compoundwas sprayed directly onto the soil surface in flats or pots. The flatsor pots were placed in a greenhouse and then watered. For postemergencetests, seeds were allowed to germinate and grow for 10 to 21 days beforeapplication. The test plants were selected for uniformity, slize, andstage of development. The test plants were then treated with the testcompound, returned to a greenhouse and watered. Untreated plants wereused as a comparison.

The compound to be evaluated was dissolved in an appropriate solvent,usually acetone, or a formulation of the evaluated compound as describedabove, was added to water, and sprayed over the flats or pots using acarrier volume equivalent to 187 or 468 liters per hectare to give arate of application in grams per hectare (g/ha). About two or four weeksafter application of the test compound, the state of the plant wasobserved. Each species was evaluated on a scale of 0-100 in which 0equals no activity and 100 equals total control. Some of the testresults are shown in Table 3

TABLE 3 Herbicidal Activity Test Results of3-Phenyl-1,2,3-Benzotriazin-4-ones (pre/post) (1200 g/ha) No BYG FOX MATOM VEL 1 0/0 0/0 0/0 0/0 0/40 2 0/15 0/0 0/0 0/15 0/60 5 0/0 0/60 0/00/0 0/30 9 0/0 0/20 0/0 0/0 0/0 14 0/0 60/0 0/0 0/0 0/0 15 0/0 75/0 0/00/0 0/0 18 0/0 0/0 0/0 0/15 0/98 19 0/10 0/0 0/0 0/50 0/90 22 0/0 0/00/0 0/0 0/80 24 0/0 0/0 0/0 0/0 0/70 26 10/98 98/90 0/0 60/95 15/100 2720/0 20/0 0/0 10/10 10/80 28 0/0 0/0 0/0 0/0 0/80 31 0/0 0/0 0/0 10/010/0 33 0/20 0/0 0/0 0140 0/100 34 0/0 0/0 0/0 0/80 0/80 35 0/0 0/0 0/00/0 0/40 36 0/70 90/50 0/0 0/25 80/100 37 20/99 100/98 0/100 100/10085/100 38 0/0 0/0 0/0 0/20 0/80 39 0/75 0/90 0/0 0/100 0/100 40 0/600140 0/80 0/85 0/100 42 0/60 0/30 0/0 0/100 0/100 43 0/80 0/85 0/0 0/200/100 44 0/80 0/95 0/95 0/80 0/100 46 0/0 0/0 0/0 0/85 0/90 49 0/0 0/00/0 0/0 0/20 50 0/0 0/30 0/0 0/85 0/70 51 95/95 80/95 0/80 85/90 80/10052 80/80 80/80 20/95 90/95 60/95 53 60/85 100/100 0/100 100/100 100/10054 80/70 90/95 0/80 100/100 100/100 55 30/90 80/90 20/100 70/100 100/10056* 0/60 20/6 — — 40/100 57 85/60 30/0 0/0 100/90 100/100 58 20/80 80/950/85 90/90 20/100 59* 60/80 100/80 — — 100/100 60 85/90 90/95 0/80100/100 100/100 61 30/90 85/20 0/60 20/80 100/100 62 95/85 90/95 60/10090/90 90/100 63 0/70 95/60 0/80 80/80 0/100 64 20/90 70/90 0/90 90/950/95 65 20/95 60/30 0/0 60/80 40/100 66 30/90 90/95 0/30 90/90 0/100 6795/95 85/90 20/70 70/100 100/100 68 95/95 20/30 0/0 20/95 70/100 6930/95 0/90 0/30 0/60 40/100 70 30/85 80/90 0/15 99/95 20/95 71 20/8590/80 0/90 100/95 0/100 72 95/80 95/95 20/100 100/100 100/100 73 20/8090/30 0/0 0/40 0/95 74 0/0 0/0 0/0 0/0 0/40 75 0/60 0/0 0/0 0/70 0/70 760/0 0/0 0/0 0/0 0/60 78 0/0 0/30 0/0 0/20 0/80 *600 g/ha

We claim:
 1. A compound of the formula:

wherein m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloakyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy substituted with halo, (C₁-C₃alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; X₁is hydrogen, halo, or acetyl; X₂ is hydrogen or halo; X₃ is halo, cyano,or nitro; X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)akynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkyamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy; and X₅ is hydrogen or halo; or wherein: a)X₁ is halo or acetyl, X₂ and X₅ are hydrogen, and X₃ and X₄ form a 5- or6-membered heterocyclic ring fused to the phenyl ring structure to forma bicyclic moiety having the structure

wherein L is oxygon (O) or sulfur (S); R₂ is hydrogen or alkyl; R₃ ishydrogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, (C₁-C₆)alkoxyalkyl, (C₃-C₆)alkenyloxyalkyl,(C₃-C₆)alkynyloxyalkyl, cyanoalkyl, amino, or hydroxy; R₄ is hydrogen,(C₁-C₃)alkyl, or fluorine; or b) X₁ and X₃ are halo, X₂ is hydrogen, andX₄ and X₅ form a 5- or 6-membered heterocyclic ring fused to the phenylring structure to form a bicyclic moiety having the structure

wherein Y is oxygen, sulfor or a group of —NR₆ in which R₆ is hydrogen,(C₁-C₆)alkyl, (C₃-C₅)alkenyl or (C₃-C₆)alkynyl; Y′ is oxygen, sulfor, agroup of —NR₆, or a group of —CO; R₅ is hydrogen, halo, (C₁-C₆)alkyl,(C₃-C₆)cycloalkyl, (C₂-C₆)alkenyl, or (C₃-C₆)alkynyl, (C₁-C₆)haloalkyl,(C₁-C₆)alkoxy, cyano, (C₁-C₆)hydroxyalkyl, a group of —CO₂R₈, a formylgroup, an acyl group, (C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, or a carboxyl group; R₆ is hydrogen,(C₁-C₆)alkyl, (C₃-C₆)alkenyl, or (C₃-C₆)alkynyl; R₇ is hydrogen, halo,(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, an acyl group, or nitro; provided thatwhen X₁ is halo and X₂ and X₃ are hydrogen or halo, then X₄ and X₅ areother than hydrogen, halo, (C₁-C₈)alkyl, or (C₁-C₄)haloalkyl; and theagronomically acceptable salts thereof.
 2. The compound of claim 1,wherein: m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy substituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; X₁is hydrogen, halo, or acetyl; X₂ is hydrogen or halo; X₃ is halo, cyano,or nitro; X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkylamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy; and X₅ is hydrogen or halo; andagronomically acceptable salts thereof.
 3. The compound of claim 1 ofthe formula:

wherein m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy substituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; Lis O or S; X₁ is H, Cl or F R₂ is H or (C₁-C₃)alkyl; and R₃ is(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl, halo(C₃-C₆)alkenyl,(C₃-C₆)alkynyl; halo(C₃-C₆)alkynyl, alkoxyalkyl; alkenyloxyalkyl;alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; and agronomicallyacceptable salts thereof.
 4. An herbicidal composition comprising one ormore compounds of claim 1 and an agronomically acceptable carrier. 5.The herbicidal composition of claim 4, wherein the compound is of theformula:

wherein: m is from 1 to 4; R₁ is hyrogen, halo, (C₁-C₄)alkyl,(C₁-C₈)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy subitituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; X₁is hydrogen, halo, or acetyl; X₂ is hydrogen or halo; X₃ is halo, cyano,or nitro; X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkylamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy; and X₅ is hydrogon or halo; provided thatwhen X₁ is halo and X₂ and X₃ are hydrogen or halo, then X₄ and X₅ areother than hydrogen, halo, (C₁-C₈)alkyl, or (C₁-C₄)haloalkyl; andagronomically acceptable salts thereof.
 6. The herbicidal composition ofclaim 4, wherein the compound is of the formula:

wherein m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy substituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; Lis O or S; X₁ is H, Cl or F R₂ is H or (C₁-C₃)alkyl; and R₃ is(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl, halo(C₃-C₆)alkenyl,(C₃-C₆)alkynyl; halo(C₃-C₆)alkynyl, alkoxyalkyl; alkenyloxyalkyl;alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; and agronomicallyacceptable salts thereof.
 7. A method for controlling unwantedvegetation comprising applying to the unwanted vegetation, or to thesoil wherein the unwanted vegetation grows, an herbicidally effectiveamount of one or more compounds of claim 1 or the composition of claim4.
 8. The method of claim 7, wherein the compound is of the formula:

wherein: m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phenoxy substituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; X₁is hydrogen, halo, or acetyl; X₂ is hydrogen or halo; X₃ is halo, cyano,or nitro; X₄ is halo, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₃-C₆)cycloalkoxy, (C₂-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₃-C₆)alkynyloxycarbonyl, (C₁-C₈)alkylsulfonylamino,(C₁-C₈)alkylsulfonylalkylamino, (C₁-C₄)alkoxycarbonylmethoxy, or(C₁-C₄)alkoxycarbonylethoxy; and X₅ is hydrogen or halo; andagronomically acceptable salts thereof.
 9. The method of claim 7,wherein the compound is of the formula:

wherein m is from 1 to 4; R₁ is hydrogen, halo, (C₁-C₄)alkyl,(C₁-C₃)haloalkyl, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, nitro, cyano,phenoxy, or phonoxy substituted with halo, (C₁-C₃)alkyl,(C₁-C₃)haloalkyl, nitro, (C₁-C₃)alkoxy, (C₁-C₃)haloalkoxy, or cyano; Lis O or S; X₁ is H, Cl or F R₂ is H or (C₁-C₃)alkyl; and R₃ is(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl, halo(C₃-C₆)alkenyl,(C₃-C₆)alkynyl; halo(C₃-C₆)alkynyl, alkoxyalkyl; alkenyloxyalkyl;alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; and agronomicallyaeceptable salts thereof.